The present invention relates to the field of surface active agents produced from by-products of papermaking.
Most aldehydes are known to react with sodium bisulfite in aqueous solution to produce an aldehyde-bisulfide complex according to reaction (I) as follows: ##STR1##
The aldehyde bisulfite complex is known to react with primary and secondary amines, to form disulfonates and sulfonates, according to the following reactions (II) and (III): ##STR2##
In the above reactions, R is generally hydrogen, short chain alkyl- or aryl-, and R.sub.1, R.sub.2 are generally alkyl-, aryl-cycloalkyl-, alkenyl-, benzyl-, or hydroxyethyl-, or sulfoethyl-.
Amides are also known to react with the aldehyde bisulfite complex. Sulfomethylated long chain (C.sub.12 -C.sub.19) amides are known as detergents and have been manufactured in Germany under such trademarks as ODA IGEPON, HO 1/81, and LUWIPAL R. These materials are prepared by reacting a solid fatty amide with the addition product of sodium bisulfite and formaldehyde at 210.degree. C., according to reaction (IV): ##STR3##
A representative discussion of the preparation of such materials is given in U.S. Pat. No. 3,047,509.
Sulfomethylation products of stearic acid - triethylene tetramine condensates are disclosed in Swiss patent No. 571,474. These products are described as dying assistants, fat-liquoring agents for leather, plasticizers and antistatic agents for paper.
It was earlier reported (U.S. Pat. No. 4,561,901) that the reaction product of polyamines and certain polycarboxylic acid anhydrides, when subsequently sulfomethylated with formaldehyde and bisulfite, can be employed as amphoteric emulsifiers for anionic and cationic bituminous emulsions. The polycarboxylic acid anhydrides are first formed by reacting maleic anhydride with oleic acid, elaidic acid, or conjugated or non-conjugated linoleic acid.
It also was reported (U.S. Pat. Nos. 4,494,992 and 4,478,642) that the reaction product of polyamines and certain polycarboxylic acids and sulfonated carboxylic acids, when subsequently sulfomethylated with formaldehyde and bisulfite, can be employed as amphoteric emulsifiers for anionic and cationic bituminous emulsions. The certain polycarboxylic acids are the C.sub.19 - and C.sub.21 -dicarboxylic acids and C.sub.22 -tricarboxylic acid formed by reacting oleic acid, elaidic acid, and conjugated linoleic acid with acrylic acid, methacrylic acid, fumaric acid or maleic acid.